Synthesis of novel dispiro[acenaphthylene-pyrrolidine-pyrrolisine] derivatives via a 1,3-dipolar cycloaddition of azomethine ylide

Abstract

2,3-Dihydro-1H-pyrrolisin-1-one was reacted with aromatic aldehyde to give (E)-2-arylmethylidene-2,3-dihydro-1H-pyrrolisin-1-ones. A 1,3-dipolar cycloaddition of azomethine ylide generated in situ from acenaphthenequinone and sarcosine with (E)-2-arylmethylidene-2,3-dihydro-1H-pyrrolisin-1-ones gave novel 4′-aryl-1′-methyl-1″H,2H-dispiro [acenaphthylene-1, 2′-pyrrolidine-3′,2″-pyrrolisine]-1″,2-diones in moderate yields. The structures of all the products were characterised by NMR, IR, MS and the stereochemistry of the dispiro[acenaphthylene-pyrrolidine- pyrrolisine] derivatives was confirmed by X-ray crystallography.